Parties to a dispute that goes to court typically seek to retain the best lawyer they can afford. But do the ‘best’ lawyers get better results? This article surveys the literature across various jurisdictions before introducing a recent study of determinants of litigation outcomes in Singapore. The focus is on whether there is a correlation between various measures of lawyer quality (size of law firm, professional status, years of experience, etc) and actual success in court. Consistent with past studies, larger and better-resourced law firms tend to do better on average — though Singapore is unusual in that the Government Legal Service functions like the largest and best-resourced law firm. Individual lawyers, however, yield unusual results, with more experienced lawyers sometimes having a lower success rate in court — perhaps due to them taking on more complex cases. The study also shows that women are significantly underrepresented as lead counsel in Singapore, but on average may outperform men.